


The Best Valentine’s Day Ever

by dodger_sister



Category: Supernatural
Genre: + Some Cameos, Alternate Universe, Alternate Universe - Middle School, First Kiss, Fluff, Holidays, M/M, Mild Language, Romance, Valentine's Day, Wee!chesters, Weechesters
Language: English
Status: Completed
Published: 2021-02-12
Updated: 2021-02-12
Packaged: 2021-03-12 11:14:58
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,480
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29384007
Author URL: https://archiveofourown.org/users/dodger_sister/pseuds/dodger_sister
Summary: Dean wants to buy something special for someone special for Valentine’s Day. First he needs to figure out what to buy, where to get the money and which special classmate to give it to.
Relationships: Castiel/Dean Winchester
Comments: 4
Kudos: 16





	The Best Valentine’s Day Ever

**Author's Note:**

> Written early-2012.  
> Beta’d by the awesome [Liptonrm](https://archiveofourown.org/users/liptonrm)  
> 2021 Note: Written before Charlie Bradbury was a thing in canon. This Charlie is from my friends’, Baylor & Liptonrm, alternate canon creation, SuperPretendNatural - used with permission, ofc. Unfortunately the website link has long since expired, but just imagine a 12 year old Jason London.  
> Happy Valentine's Day, everyone!

Being twelve was hard.

That was something Dean’s father just didn’t understand. There was a lot of pressure on him.

Like, take for instance, the upcoming Valentine’s Day party at school. His teacher had told them they had to give out cards to everyone in the class. It was the sixth grade and Dean thought they were a little old for those stupid Valentine’s Day cards that come in the box with all the various cartoon characters on them, but his teacher was some sort of hippie or something and thought everyone deserved love on this special holiday.

When Dean made this remark to the girl who sits next to him, Sally, she pointed out that true hippies wouldn’t celebrate such a commercial holiday in the first place.

Anyways, Dean had figured it wasn’t any big deal – his dad was used to having to pick up those boxed cards for him for school, and of course he would have to buy some for Sammy too, which would make the blow of demanding their dad spend money a little easier. Sammy had this way of getting John to be happy about wasting money on stupid things.

So that was all settled, until Dean’s friend Charlie had pointed out what a great opportunity this could be for them.

“Look, spend a little money on something nice for a girl and she is totally going to give you some,” Charlie said, his patented smirk fully in place.

“Some what?” Dean asked, because even Charlie wasn’t stupid enough to think any girl was putting out for a teddy bear.

“Tongue,” Charlie told him, like Dean was ridiculous for not knowing that. “Give a girl some chocolate, make her feel special, get a little tongue in return.”

“Where do you come up with this garbage?” Dean asked him, but later he thought about it.

There were a couple of girls in Dean’s class he wouldn’t mind calling his girlfriend, though he wasn’t sure what that entailed exactly – passing notes and holding hands and sitting together at lunch seemed to be the norm. But the thing was, he could probably only afford to buy _one_ thing for _one_ girl – if that even – and Dean had to decide who.

And he had to find a way to get some money on top of it all.

Yep, being twelve was hard.

***

Dean trudged into the back of the auto shop and knocked on the open office door.

Bobby looked up from his stack of paperwork. “Hi, kiddo. How was school?”

Dean shrugged and waited for Bobby to fish around in the desk, pull out a small package of crackers and toss them to him.

“Got any cookies in that desk?” Dean asked, but wasn’t surprised when Bobby just glared at him. John had kind of chewed the man out for getting Sammy all jacked up on sugar one day and now Bobby was on this health kick that was killing Dean.

“Where’s your brother?” Bobby asked.

“Telling Caleb about the magic frog.”

“Come again?” and he was looking at Dean with one raised eyebrow.

“I dunno, something in some book they read at school.”

Bobby smirked. “Well, I’m sure Caleb is enjoying that immensely.”

Dean came a little farther into the office and slumped down in the old red chair with a dramatic sigh.

“Somethin’ on your mind, boy?” Bobby asked and made Dean’s day when he pulled a box of cookies out of the desk and handed them over.

Dean took a cookie from the box, bit into it and chewed slowly, mulling over the answer.

“I suppose I have a girl problem,” he said at last and Bobby looked both amused and horrified. “See, the thing is, if I want to buy something special, you know, like for _someone_ special, I need money. Only Dad’s not going to be happy about buying those stupid cards for the whole damn class…”

“Language.”

“Sorry…and there is no way he’ll give me any extra and I need some extra, Uncle Bobby. You know, for Valentine’s Day.”

“You got someone special in mind?” Bobby asked, because Dean regularly changed which girl he liked and Bobby couldn’t keep up anymore.

“I dunno. I mean, I got a few people in mind. I just gotta play my cards right and pick the right one.”

“Somehow I think this is all Charlie’s influence,” Bobby grumbled, but that didn’t stop him from helping Dean out, in the end.

***

Dean vacuumed Bobby’s house and wiped down all the surfaces he could reach and hand-washed all the good plates.

“Break any of ‘em and you’ll need a day job just to pay me back, got it?” Bobby growled at him.

“How come you want the house so clean?” Dean asked.

“Got company coming over on Wednesday,” Bobby told him and helped him shove the vacuum back in the over-crowded closet.

“Isn’t Wednesday Valentine’s Day? Who you got comin’ over on Valentine’s Day?” Dean said with the kind of grin that usually got him whacked on the back of the head.

“How about you mind your own damn business, boy?” Bobby said, turning a smidge red and stomping upstairs.

But later, he gave Dean enough money to buy the perfect present for the perfect someone.

***

The next day, Dean pulled Charlie aside on the playground and said, “I have enough money for two things, I think. What are you getting?”

“I dunno. I figured I’d let my sister pick out whatever she likes and go with that,” Charlie told him.

Dean kind of couldn’t stand Charlie’s sister, so that was really no help at all.

“I’m getting Spiderman cards,” Ash told them and that wasn’t really helpful either. Or surprising. Ash wore his Spiderman shirt almost every day. It was kind of gross.

“Well, I’m getting _Barbie_ cards,” Calvin said. “Because that’s what the girls like.”

“Or that’s what _you_ like,” Pamela replied and everyone laughed. 

“I’m getting Last Airbender cards,” Castiel said quietly and looked surprised when Pamela offered him a high-five for that.

“My mom is sending homemade sugar cookies,” Andy told them all and everyone nodded enthusiastically. Andy’s mom always made the _best_ cookies.

But then Charlie threw the soccer ball into the middle of the field and everyone quickly got distracted with a game.

So Dean was surprised later, when Cas came up to him and asked, “Are you getting Batman cards again this year, Dean? It’s _Batman_ you like, right?”

Dean was half-surprised because they had let the Valentine conversation go as soon as the soccer ball had hit the field. And the other half-surprised because Cas _never_ spoke to him. They’d been in the same class for a grade and a half and Cas had never voluntarily said anything to Dean beyond, “Do you have a pencil?”

The longest conversation they had ever had was when Dean had stopped him outside the school and asked Cas a question about what chapter they were supposed to be reading in their history book and Cas ended up giving him an impassioned speech about how brothers had to fight against each other in the Civil War. It’d lasted nearly four minutes and Cas had been so fired up, he had started dropping the ‘ _g_ ’s off the end of his words and when it was over, Cas had turned bright red and run off in the opposite direction from where Dean was headed, which also happened to be the opposite direction from where Cas lived.

But now, here was Cas, quiet scrawny little Cas, voluntarily striking up a conversation with him.

Dean stood up from where he had been tying his shoe. “Batman? Yeah, I don’t know if I’m getting Batman cards again this year. I may go with The Avengers, just to mix it up. But I mean, Batman is still the most badass superhero there is,” and Dean looked around real quick, just to make sure no teachers had heard him curse.

Cas was sort of looking down at his shoes, sneaking a little peak at Dean. “I just wondered if you still liked Batman, is all,” and it was so quiet Dean could barely hear him.

“Yeah, dude, Batman is The Man - that’s why they call him _The Bat Man_.” It was a funny joke, so Dean winked at Cas during the punch line.

Cas just nodded three very quick jerky nods and said, “Okay,” before running off in the opposite direction.

***

After school, Dean walked to the store and picked out a box of chocolates and a stuffed blue teddy bear. He spent all but 30 cents of his money and shoved the gifts way down in his bag so none of the guys at the garage would see them and start teasing him.

But he was nervous and kind of excited, because he’d never done anything special for Valentine’s Day before, so when he picked Sammy up from school, he pulled the presents back out and showed them to his little brother.

Sammy had a sugar kick like nobody Dean had ever met, so the first words out of his mouth were, “Can I have a chocolate?”

“No, Sam, it’s a _present_.”

“For who?”

Dean shrugged and shoved the chocolate back in the bag before Sam got too grabby. “I haven’t decided yet.”

“Is the bear’s name Rupert?” Sam asked and grabbed it up in his arms.

“Why would his name be _Rupert_?”

“You know, like in the book.”

“That’s Paddington.”

“Not _that_ book!” but Sam’s outcry was muffled because he had shoved his face into the bear’s stomach and was rubbing it against his cheek.

“Stop getting your slobber all over it,” Dean snapped and grabbed the stuffed animal back, shoving it down inside his bag. “I just wanted to get something nice for someone,” he said a little sullenly, because he was starting to think this was another one of Charlie’s ideas that was going to backfire on him, like the thing with the firecrackers and the shoe.

Sam gave Dean the big puppy eyes of hurt, but still said, “I liked the bear, Dean. I think Rupert’s very nice and he’d make a good friend.”

“Thanks, Sammy,” and Dean half-smiled at his little brother. “Just don’t tell no one, okay?” and he tugged Sam along behind him.

***

Dean was sitting at the kitchen table filling out his Valentines in as neat of hand-writing as he could muster – per the teacher’s instructions – when John came in and pulled a beer out of the fridge.

He tapped Dean on the head and said, “Hey kiddo, don’t look so disgruntled about spreading love, okay?”

Dean just scowled down at the stack of cards. “It’s ridiculous, Dad. There are like twenty-three kids in my class. That’s a damn lot of cards.”

John whacked Dean on the back of the head before settling in the chair opposite him. “Watch your mouth.”

“Sorry. But…don’t you think I’m a little old for this?”

John shrugged. “I dunno. But look at it this way – there will be cookies and candy and no schoolwork for like a whole hour, right? So, enjoy that.”

Dean figured his dad was probably right about that. He flipped through his stack of cards, looking for the perfect one for Sally. He decided on Thor swinging his hammer and saying, ‘ _You make my heart hammer_ ’.

“But,” Dean started again, because his dad was still sitting there, looking through the cards Dean had already filled out, “don’t you think it’s a little weird for me to give cards to other boys? Or, like, boys I don’t even really like that much, like Zach. I mean, come on, that guy is a dillhole.” Dean braced himself a little to see if he’d get in trouble for the word _dillhole_ , but John didn’t call him on it.

Instead John said, “Well, maybe all Zach needs to not be such a _dillhole_ ,” and John raised an eyebrow at Dean so he knew that one hadn’t slipped past him, “is for someone to show him a little love.”

“Yeah, Dad, sure. A card showing Captain America holding a heart instead of a shield is all Zach needs to completely turn his life around. Good call.”

“Smart-mouth,” John muttered.

Dean pulled out the next card – Hawkeye shooting an arrow through a pink heart – and started filling in Pamela’s name.

“You know,” John said after a moment of silence, “it’s okay if you give Valentines to boys.”

Dean’s head jerked up a little at that. “What?”

John took a swallow of his beer. “It’s just…it’s not…it’s not really my thing but you know, it’s a new millennium and you are of a new generation and I guess those things aren’t that big of a deal these days.”

“Dad, seriously…”

“I’m just…I’m just saying, it’s okay with me.”

Dean wanted to say something really sarcastic and smart-mouthed, but he could tell it took a lot for his dad to say that, so Dean just nodded and went back to Pamela’s card.

John got up then, headed over to the counter to start dinner.

“Hey, Dad?”

“Hmmm?”

“How do boys have sex with other boys? Like, where does everything _go_?”

John choked then, on his own spit or beer, Dean wasn’t sure. His face turned red and he sputtered out something that may have been the word ‘ _what_ ’.

“Dude,” Dean said with a smirk, “you should see your face right now. It’s _awesome_.”

John swallowed the last of his beer and pointed a finger at Dean. “That isn’t even a little bit funny, Dean.”

“It’s a _little_ funny.”

“You just…you just finish your cards and then help Sammy with his. Got it?”

“What?!” Dean cried. “Why do I have to help Sam? He can do it himself.”

“Dude,” John said with a grin, “you should see your face right now. It’s _awesome_.”

“Not funny, old man. So I don’t have to help Sammy with his?”

“Oh no, you _do_ have to. All _twenty-three_ of them.”

Dean turned back to his stack of cards. Valentine’s Day was _so_ not worth this.

***

The school party was pretty lame – much as Dean had expected – but Andy’s mom made sugar cookie hearts with pink frosting that were delicious and the teacher gave them twenty minutes of free time, so it wasn’t a total waste.

Dean had gotten a couple of really fancy cards from some of the girls. One had nearly a hundred pink hearts drawn all over it, while another had so much glitter in the envelope that it stuck to Dean’s jeans and he couldn’t get the glitter off for the rest of the day. And Pamela gave him a postcard that had a picture of Jimmy Page on it, which was _awesome_.

“I’m not hitting on you,” Pamela told him, when Dean went over to her desk to tell her ‘ _thank you_ ’.

“Oookay,” Dean said slowly. “That hadn’t actually occurred to me, but now that you mention it,” and he smiled at her with his best leer, which wasn’t a very good leer, really. He was still only twelve, after all.

“Knock it off,” she told him. “I just saw it and I didn’t want to have to wait until like Christmas to give it to you. Just be cool about it, would you?”

Dean thought about the box of chocolates and the teddy bear stuffed inside his desk, but Pamela would laugh at such girly gifts and anyways, she wasn’t hitting on him. 

“Then I’ll just get you something awesome next month for your birthday,” he said instead.

“You better. My dad is taking us to play paintball.”

Dean went back to his desk and put the Zeppelin card inside his math book so it wouldn’t get wrecked. He sat down then and went through his stack of cards one more time.

Dean counted three Barbie cards, two Disney Princesses, two Twilights, three Scooby-Doos, two Pixar Cars, one Shrek, one with pirates and about seven with varying degrees of superheroes on them. When he counted, he came up short by one and it suddenly occurred to him that there wasn’t an Avatar: The Last Airbender card in there from Castiel, which he had kind of been looking forward too. Dean had all the seasons on DVD – he’d saved up for _months_ for those.

He wondered what had happened that he hadn’t gotten a card from Cas. He knew Cas had given out cards, because Dean had seen him walking around the classroom, passing them out. Maybe it was an accident. Maybe Cas had overlooked him somehow. Dean hoped that was it. He hoped Cas wasn’t mad at him for something, even though Dean had no clue what Cas could be mad at him about.

And if Dean asked Cas about it, the other boy would just be embarrassed and upset to think he had forgotten to give Dean a card.

Though, honestly, Dean was kind of surprised to realize how upset _he_ was that Cas hadn’t given him a Valentine’s card, which was ridiculous, so Dean decided to just not think about it.

Charlie came over then and plopped down right on top of Dean’s desk.

“Watch your smelly butt,” Dean told him and shoved him over before all the Valentine’s cards fell on the floor.

“Tony Stark is the king of all things,” Charlie said and Dean would have thought it was coming out of left field, except he had given Charlie the best Iron Man card in the whole box and then made sure that no one else got one like it.

“Batman is better,” Dean said because it was an old, familiar argument between them.

“Here,” Charlie said and thrust a handful of Batman pencils at him. “They came with the DC cards I got for all the boys, but there weren’t any pencils in with the stupid cat cards I got the girls, so it wasn’t really fair for me to give pencils to the boys and not the girls.” Charlie was talking kind of fast and Dean realized he was embarrassed. “It’s not a Valentine’s present though,” he added.

“Thanks, man,” Dean said and tried to play it off, so Charlie could save some face.

Charlie shrugged. “It’s cool,” he said and slapped Dean on the shoulder, before going back to his desk.

Dean took his new pencils up to the sharpener at the front of the room then. He broke in two pencils and when he turned around, Castiel was standing there, staring at him with wide blue eyes.

“Hello, Dean,” he said.

“Hey, Cas,” Dean answered and tried to step around the other boy.

Cas held up his hand and Dean stopped.

“I got you something,” Cas said so quietly that Dean almost didn’t hear him.

“Okay,” Dean said, even though he wasn’t exactly sure what was happening.

“It’s probably stupid,” Cas told him and he wasn’t quite looking at Dean while he talked, but Dean could still see the blush spreading across the other boy’s face. “I mean, teddy bears are for girls and it’s probably dumb and you can tell me if it’s dumb but… _here_ ,” and Cas held up a teddy bear for Dean to see.

It was a small bear and he was dressed in a Batman outfit.

To be honest, it _was_ kind of dumb. Dean was twelve and a boy and teddy bears weren’t really his thing. But even from here, Dean could tell that the Batman outfit was handmade.

Cas had made it himself.

For Dean.

And that was kind of not-so-dumb.

Dean reached out to take the teddy bear. Their fingers brushed together then and Cas’ hand was warm and soft. Dean studied the teddy bear carefully and then smiled at Cas. “Thanks, Cas. I love it.”

“You’re welcome,” Cas said and Dean didn’t miss the smile that crept across his face.

Dean put the teddy bear on his desk next to the pencils and the stack of Valentine’s cards. He figured he should be embarrassed by it, but for some reason he just felt warm and good. And anyways, the only person who would dare tease Dean about the teddy bear was Charlie, and he wouldn’t really mean it.

***

Dean was sliding into his jacket for recess when Charlie came up behind him.

“Dude, you didn’t give out your presents yet.”

“I can’t decide,” Dean said sullenly, because this was a hard decision to make. He looked at the teddy bear and the box of chocolates, sitting on the floor of his locker now.

“It’s not that big of a deal,” Charlie said and winked over at Anna, who gave him a confused look and turned back to her friends.

“Yeah, Anna looks totally blown away by the Hello-Kitty hairclips you bought her,” Dean said with a smirk. “Of course, that may be because you also bought some for Ava and Sally too, but whatever.”

“Shut it,” Charlie grumbled. “At least I’m not afraid to go for it, you wuss.”

Dean would have had a comeback for that, except Charlie was kind of right. He picked up the box of chocolates and stuffed them inside his jacket.

It was time to man-up.

***

It took him a few minutes to find Cas on the playground. The other boy was back behind the tree-line, where they weren’t supposed to go, but sometimes they did anyways just to see if they could get away with it.

“Hey, Cas,” Dean said and Cas jerked in surprise.

“Hello, Dean,” he said. “I’m not hiding.”

“Okay.”

“I thought…I thought maybe the other boys might make fun of me for giving you a teddy bear.”

“But it’s a _Batman_ bear. That’s totally hardcore,” which okay, maybe it wasn’t, but Dean didn’t want Cas to think he had to be ashamed of the present, especially since Dean liked it so much.

“I liked The Avengers card you gave me,” Cas said. “Because it had the whole team on it and they work the best as a team.”

“You like The Avengers?”

“Of course. I am versed in pop culture.”

Dean smiled. “Okay. I got you something,” he added and it wasn’t _totally_ true, since he hadn’t bought the gift specifically for Castiel, but it was close enough to the truth anyways.

Cas looked a little shocked, his eyes blown kind of wide and his lips slightly parted. “Like, a _present_?” he asked.

“Yeah,” and Dean pulled the box of chocolates out of his coat. “It’s not the biggest sized box, but it’s not the little box either.”

Castiel reached out and took the chocolate and Dean felt a little flutter in his heart, even though this time their fingers didn’t even touch.

“I, uh…my little brother wanted to eat them but I wouldn’t let him. He has a terrible sweet tooth,” Dean said, because Cas wasn’t saying anything and he suddenly felt odd and awkward.

Cas opened the box and was staring in at the chocolate like he had never seen anything so grand in his life.

“I don’t know if you are allowed candy,” Dean said, not completely sure of himself, which he was sure had never happened to him before.

“Thank you, Dean,” Cas said softly and then looked up, met Dean’s eyes. “ _Thank you_.”

“It’s cool, man,” Dean said and shrugged like it was no big deal, even though he kind of felt like he could explode from warmth and he wasn’t even sure why.

“Would you like a chocolate?” Castiel offered him and Dean reached in and took one.

“Thanks,” he said, then chewed it slowly. “What’d you get?” Dean asked, while Cas ate his own piece. “Mine was dark chocolate caramel.”

“Cherry filling,” Cas told him.

Cas had a bit of cherry cream on the corner of his mouth and it looked delicious and Dean’s heart was sort of flipping and hammering in his chest.

“You have some on your mouth,” Dean said and then leaned in before he could lose his nerve and kissed Castiel.

He sort of missed his mark a little and ended up catching half of Cas’ mouth and half of his cheek. And Cas must have decided to try to lick the cream off right at that moment, because just the tiniest little bit of his tongue came out at the last second. Dean wasn’t sure if that counted as french-kissing, but he was going to say it did when he told Charlie about it later.

The kiss was over before Dean could really register what had happened, but his heart was still pounding super fast and his palms were all sweaty and Cas was making the best face ever, eyes half-closed and lips slightly parted, and the only thing Dean knew for sure was that he wanted to do that again.

“Would you like another chocolate?” Castiel asked him and his voice was shaking, but he was smiling and Dean was smiling too.

“I’d love one. Thanks, Cas.”

And okay, Valentine’s Day was _so_ worth it.

***

Dean smiled pretty much the rest of the day and even his little brother being jacked up on sugar after school didn’t ruin his day.

“Hey, Sammy,” he said and stopped his brother’s rambling about each and every Valentine’s Day card he had gotten at his school party.

“What?” Sam asked, eyes scrunched up at Dean in the afternoon sunlight.

“I got you something for Valentine’s Day.”

“No foolin’?” Sam asked.

“No foolin’, buddy,” Dean said and reached into his backpack.

The blue stuffed bear had been kind of squished under all of Dean’s textbooks and homework but when he pulled him out, Sam squealed in delight.

“Rupert is for me?!” he cried and grabbed the bear up in his arms.

“I thought he needed a good home and nobody could love him better than you,” Dean told him.

“I _do_ love him, Dean. Thank you,” and Sam looked at the bear like it was the best thing he’d ever gotten in his life. Then Sam crouched down to rummage around in his own bag. “I made you something,” he said when he stood up.

Sam handed Dean a picture frame made of popsicle sticks – painted blue with green hearts all over – and in the middle of the frame was a photo of Sam and Dean sitting on the hood of some old beat-up truck in the salvage yard at Bobby’s house.

“Uncle Bobby helped me with the picture but I did the rest at school,” Sam told him and he looked so proud of himself.

“It’s perfect, Sammy. I love it.”

Sam hugged Rupert to his chest and smiled up at his big brother. “This is the best Valentine’s Day ever!”

Dean had to agree.

It was definitely the best Valentine’s Day _ever_.

The End

**Author's Note:**

> I came up with the scene where Cas gives Dean his present and then the scene where Dean gives Cas the chocolate. That’s what the story was supposed to be. I have never added so much to a story while writing before. I even went back and added more scenes after the fact. It went from what would have been about 1,200 words to over 4,000 words. I don’t know what happened, but I am seriously happy with the result. Also, I am glad I added wee!Sammy, because he is always so much fun to write.  
> For all the Lovelies on my Flist for Valentine’s Day. You guys are all awesomesauce!


End file.
